data_2203269
loop_
_publ_author_name
'Zhang, Xiu-Lian'
'Chen, Xiao-Ming'
'Ng^a^, Seik Weng'
_publ_section_title
;
 Guanidinium 4-hydroxy-3-carboxybenzene sulfonate
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o453
_journal_page_last             o454
_journal_volume                60
_journal_year                  2004
_chemical_formula_moiety       'C H6 N3 1+, C7 H5 O6 S 1-'
_chemical_formula_sum          'C8 H11 N3 O6 S'
_chemical_formula_weight       277.26
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
 Guanidinium 4-hydroxy-3-carboxybenzene sulfonate
;
_symmetry_cell_setting         Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              87.2050(10)
_cell_angle_beta               74.5170(10)
_cell_angle_gamma              66.2770(10)
_cell_formula_units_Z          2
_cell_length_a                 7.4072(6)
_cell_length_b                 8.6995(7)
_cell_length_c                 10.2525(8)
_cell_measurement_reflns_used  2298
_cell_measurement_temperature  298(2)
_cell_measurement_theta_max    28.0
_cell_measurement_theta_min    2.5
_cell_volume                   581.60(8)
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_data_reduction      SAINT
_computing_molecular_graphics  'ORTEPII (Johnson, 1976)'
_computing_publication_material SHELXL97
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device_type 'Bruker SMART APEX area-detector diffractometer'
_diffrn_measurement_method     '\w and \f scan'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.015
_diffrn_reflns_av_sigmaI/netI  0.023
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_l_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_number          5004
_diffrn_reflns_theta_full      27.6
_diffrn_reflns_theta_max       27.5
_diffrn_reflns_theta_min       2.1
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 0
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.304
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type None
_exptl_absorpt_process_details ?
_exptl_crystal_colour          Colorless
_exptl_crystal_density_diffrn  1.583
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     Plate
_exptl_crystal_F_000           288
_exptl_crystal_size_max        0.31
_exptl_crystal_size_mid        0.13
_exptl_crystal_size_min        0.05
_refine_diff_density_max       0.22
_refine_diff_density_min       -0.33
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.04
_refine_ls_hydrogen_treatment  refall
_refine_ls_matrix_type         full
_refine_ls_number_parameters   207
_refine_ls_number_reflns       2564
_refine_ls_number_restraints   11
_refine_ls_restrained_S_all    1.04
_refine_ls_R_factor_all        0.043
_refine_ls_R_factor_gt         0.038
_refine_ls_shift/su_max        0.001
_refine_ls_shift/su_mean       <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0683P)^2^+0.0934P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.108
_refine_ls_wR_factor_ref       0.112
_reflns_number_gt              2236
_reflns_number_total           2564
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.83760(6) 0.84248(5) 0.70760(4) 0.0364(2) Uani d . 1 . . S
O1 0.6389(2) 0.9598(2) 0.69710(10) 0.0492(3) Uani d . 1 . . O
O2 0.9506(2) 0.7199(2) 0.59190(10) 0.0463(3) Uani d . 1 . . O
O3 0.9595(2) 0.9274(2) 0.73570(10) 0.0461(3) Uani d . 1 . . O
O4 0.8556(2) 0.2435(2) 0.80190(10) 0.0560(4) Uani d D 1 . . O
O5 0.7601(2) 0.2181(2) 1.02460(10) 0.0519(3) Uani d . 1 . . O
O6 0.6677(2) 0.4730(2) 1.18920(10) 0.0519(4) Uani d D 1 . . O
N1 0.3895(3) 0.8336(2) 0.6066(2) 0.0562(4) Uani d D 1 . . N
N2 0.6772(3) 0.6794(2) 0.4409(2) 0.0527(4) Uani d D 1 . . N
N3 0.3682(3) 0.6795(2) 0.4418(2) 0.0486(4) Uani d D 1 . . N
C1 0.7936(2) 0.7276(2) 0.8501(2) 0.0335(3) Uani d . 1 . . C
C2 0.8123(2) 0.5654(2) 0.8335(2) 0.0350(3) Uani d D 1 . . C
C3 0.7713(2) 0.4761(2) 0.9455(2) 0.0349(4) Uani d . 1 . . C
C4 0.7091(3) 0.5536(2) 1.0758(2) 0.0379(4) Uani d . 1 . . C
C5 0.6892(3) 0.7183(2) 1.0916(2) 0.0431(4) Uani d D 1 . . C
C6 0.7316(3) 0.8043(2) 0.9803(2) 0.0395(4) Uani d D 1 . . C
C7 0.7943(3) 0.3002(2) 0.9296(2) 0.0393(4) Uani d . 1 . . C
C8 0.4772(3) 0.7315(2) 0.4966(2) 0.0416(4) Uani d . 1 . . C
H4o 0.879(4) 0.142(2) 0.788(3) 0.087(9) Uiso d D 1 . . H
H6o 0.694(4) 0.375(2) 1.158(3) 0.084(9) Uiso d D 1 . . H
H1n1 0.263(2) 0.871(3) 0.643(2) 0.059(6) Uiso d D 1 . . H
H1n2 0.459(3) 0.873(3) 0.636(2) 0.054(6) Uiso d D 1 . . H
H2n1 0.751(3) 0.708(3) 0.477(2) 0.060(7) Uiso d D 1 . . H
H2n2 0.734(3) 0.602(2) 0.377(2) 0.072(7) Uiso d D 1 . . H
H3n1 0.425(3) 0.621(2) 0.3660(10) 0.059(6) Uiso d D 1 . . H
H3n2 0.238(2) 0.716(3) 0.478(2) 0.064(7) Uiso d D 1 . . H
H2 0.851(3) 0.512(2) 0.7470(10) 0.043(5) Uiso d D 1 . . H
H5 0.649(3) 0.771(3) 1.1800(10) 0.066(6) Uiso d D 1 . . H
H6 0.718(3) 0.9170(10) 0.993(2) 0.047(5) Uiso d D 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0411(3) 0.0286(2) 0.0400(2) -0.0164(2) -0.0074(2) -0.0028(2)
O1 0.0510(10) 0.0390(10) 0.0570(10) -0.0150(10) -0.0190(10) 0.0050(10)
O2 0.0560(10) 0.0410(10) 0.0420(10) -0.0250(10) -0.0020(10) -0.0080(10)
O3 0.0490(10) 0.0370(10) 0.0560(10) -0.0250(10) -0.0060(10) -0.0070(10)
O4 0.0870(10) 0.0330(10) 0.0510(10) -0.0310(10) -0.0110(10) -0.0060(10)
O5 0.0660(10) 0.0390(10) 0.0550(10) -0.0270(10) -0.0140(10) 0.0070(10)
O6 0.0670(10) 0.0440(10) 0.0410(10) -0.0230(10) -0.0060(10) 0.0020(10)
N1 0.0440(10) 0.0670(10) 0.0550(10) -0.0220(10) -0.0070(10) -0.0140(10)
N2 0.0450(10) 0.0630(10) 0.0500(10) -0.0240(10) -0.0070(10) -0.0090(10)
N3 0.0490(10) 0.0530(10) 0.0480(10) -0.0250(10) -0.0130(10) 0.0020(10)
C1 0.0320(10) 0.0280(10) 0.0400(10) -0.0120(10) -0.0090(10) -0.0020(10)
C2 0.0370(10) 0.0300(10) 0.0380(10) -0.0140(10) -0.0080(10) -0.0060(10)
C3 0.0330(10) 0.0290(10) 0.0420(10) -0.0120(10) -0.0090(10) -0.0040(10)
C4 0.0360(10) 0.0350(10) 0.0400(10) -0.0120(10) -0.0080(10) 0.0000(10)
C5 0.0490(10) 0.0360(10) 0.0390(10) -0.0130(10) -0.0100(10) -0.0090(10)
C6 0.0450(10) 0.0280(10) 0.0440(10) -0.0130(10) -0.0110(10) -0.0070(10)
C7 0.0390(10) 0.0310(10) 0.0500(10) -0.0160(10) -0.0120(10) -0.0010(10)
C8 0.0460(10) 0.0410(10) 0.0400(10) -0.0210(10) -0.0130(10) 0.0080(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 113.20(10) yes
O1 S1 O3 . . 112.30(10) yes
O2 S1 O3 . . 111.80(10) yes
O1 S1 C1 . . 106.60(10) yes
O2 S1 C1 . . 106.40(10) yes
O3 S1 C1 . . 105.90(10) yes
C2 C1 C6 . . 120.00(10) yes
C2 C1 S1 . . 120.30(10) yes
C6 C1 S1 . . 119.70(10) yes
C1 C2 C3 . . 120.60(10) yes
C2 C3 C4 . . 119.20(10) yes
C2 C3 C7 . . 121.30(10) yes
C4 C3 C7 . . 119.5(2) yes
O6 C4 C5 . . 118.1(2) yes
O6 C4 C3 . . 122.1(2) yes
C5 C4 C3 . . 119.9(2) yes
C6 C5 C4 . . 120.3(2) yes
C5 C6 C1 . . 120.10(10) yes
O5 C7 O4 . . 123.9(2) yes
O5 C7 C3 . . 123.3(2) yes
O4 C7 C3 . . 112.8(2) yes
N1 C8 N3 . . 120.4(2) yes
N1 C8 N2 . . 119.8(2) yes
N3 C8 N2 . . 119.8(2) yes
C7 O4 H4o . . 116(2) no
C4 O6 H6o . . 103(2) no
C8 N1 H1n1 . . 122(2) no
C8 N1 H1n2 . . 119(2) no
H1n1 N1 H1n2 . . 118(2) no
C8 N2 H2n1 . . 121(2) no
C8 N2 H2n2 . . 118(2) no
H2n1 N2 H2n2 . . 120(2) no
C8 N3 H3n1 . . 119(2) no
C8 N3 H3n2 . . 119(2) no
H3n1 N3 H3n2 . . 121(2) no
C1 C2 H2 . . 122.0(10) no
C3 C2 H2 . . 118.0(10) no
C6 C5 H5 . . 120.0(10) no
C4 C5 H5 . . 120.0(10) no
C5 C6 H6 . . 119.0(10) no
C1 C6 H6 . . 121.0(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4440(10) yes
S1 O2 . 1.4560(10) yes
S1 O3 . 1.4630(10) yes
S1 C1 . 1.762(2) yes
O4 C7 . 1.315(2) yes
O5 C7 . 1.212(2) yes
O6 C4 . 1.357(2) yes
N1 C8 . 1.313(2) yes
N2 C8 . 1.326(2) yes
N3 C8 . 1.317(2) yes
C1 C2 . 1.376(2) yes
C1 C6 . 1.397(2) yes
C2 C3 . 1.389(2) yes
C3 C4 . 1.400(2) yes
C3 C7 . 1.482(2) yes
C4 C5 . 1.393(2) yes
C5 C6 . 1.369(3) yes
O4 H4o . 0.840(10) no
O6 H6o . 0.850(10) no
N1 H1n1 . 0.840(10) no
N1 H1n2 . 0.840(10) no
N2 H2n1 . 0.850(10) no
N2 H2n2 . 0.850(10) no
N3 H3n1 . 0.860(10) no
N3 H3n2 . 0.860(10) no
C2 H2 . 0.940(10) no
C5 H5 . 0.950(10) no
C6 H6 . 0.950(10) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4o O3 1_545 0.840(10) 1.780(10) 2.611(2) 171(3) yes
O6 H6o O5 . 0.850(10) 1.80(2) 2.601(2) 155(3) yes
N1 H1n2 O1 . 0.840(10) 2.010(10) 2.851(2) 177(2) yes
N1 H1n1 O3 1_455 0.840(10) 2.050(10) 2.885(2) 172(2) yes
N2 H2n1 O2 . 0.850(10) 2.160(10) 2.988(2) 166(2) yes
N2 H2n2 O6 1_554 0.850(10) 2.52(2) 3.246(2) 143(2) yes
N3 H3n1 O6 1_554 0.860(10) 2.190(10) 3.006(2) 159(2) yes
N3 H3n2 O2 1_455 0.860(10) 2.130(10) 2.949(2) 160(2) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . 103.60(10) no
O2 S1 C1 C2 . . . . -17.6(2) no
O3 S1 C1 C2 . . . . -136.70(10) no
O1 S1 C1 C6 . . . . -73.9(2) no
O2 S1 C1 C6 . . . . 165.00(10) no
O3 S1 C1 C6 . . . . 45.9(2) no
C6 C1 C2 C3 . . . . -0.5(3) no
S1 C1 C2 C3 . . . . -177.90(10) no
C1 C2 C3 C4 . . . . 0.5(2) no
C1 C2 C3 C7 . . . . -178.8(2) no
C2 C3 C4 O6 . . . . -179.7(2) no
C7 C3 C4 O6 . . . . -0.4(3) no
C2 C3 C4 C5 . . . . 0.0(3) no
C7 C3 C4 C5 . . . . 179.3(2) no
O6 C4 C5 C6 . . . . 179.2(2) no
C3 C4 C5 C6 . . . . -0.5(3) no
C4 C5 C6 C1 . . . . 0.5(3) no
C2 C1 C6 C5 . . . . 0.0(3) no
S1 C1 C6 C5 . . . . 177.40(10) no
C2 C3 C7 O5 . . . . -180.0(2) no
C4 C3 C7 O5 . . . . 0.7(3) no
C2 C3 C7 O4 . . . . 0.0(2) no
C4 C3 C7 O4 . . . . -179.3(2) no